2,2'-Dimethylbiphenyl → 6-(4-Methylphenyl)-1,2,3,4-tetrahydronaphthalene

HRID 2212830Notes

Reaction equation

HRID 2212830 reaction equation
C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.CCCCCC[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].CO[C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][CH:44]=1)[CH2:41][CH2:40][CH2:39][CH2:38]2.C1(C)C(C2C(C)=CC=CC=2)=CC=CC=1>>[CH3:32][C:31]1[CH:26]=[CH:27][C:28]([C:35]2[CH:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:29][CH:30]=1

Participants

5

Reactant 4

HCID 117972,2'-DimethylbiphenylHCID 12388TridecaneHCID 744146-Methoxytetralin2×HCID 75806Tricyclohexylphosphine

Product 1

HCID 111487746-(4-Methylphenyl)-1,2,3,4-tetrahydronaphthaleneYield 76%

Conditions

Temperature
60 °C

Procedure

In a reaction flask was placed NiCl2(PCy3)2 (61.2 mg, 0.0886 mmol), PCy3 (49.0 mg, 0.175 mmol), tridecane (255 mg, 1.386 mmol, as an internal standard), and 6-methoxy-1,2,3,4-tetrahydronaphthalene (273 mg, 1.683 mmol). The Grignard reagent (1 M in THF, 5.0 mmol) was added to this mixture under a nitrogen atmosphere at room temperature. The resulting solution was warmed to 60° C. for 15 hours. A sample was withdrawn and quenched with an aqueous sodium citrate solution (1 M). The aqueous solution was extracted with ethyl acetate. GC analysis of the organic phase showed the presence of 6-(4-methylphenyl)-1,2,3,4-tetrahydronaphthalene (1.272 mmol, 76% yield), bitoluene (0.50 mmol), and 6-methoxy-1,2,3,4-tetrahydronaphthalene (0.357 mmol) in the reaction mixture.

Workup

  1. customIn a reaction flask was placed
  2. customA sample was withdrawn
  3. customquenched with an aqueous sodium citrate solution (1 M)
  4. extractionThe aqueous solution was extracted with ethyl acetate

Sources & evidence

ORD record
ord-af48ed315224466f8b02ca7dc677fbb7
Source dataset
uspto-grants-2006_09
Patent number
US07105467B2

Reaction notes

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